(R)-4,4-dimethyl-1-phenylpentan-3-ol | 821785-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4,4-dimethyl-1-phenylpentan-3-ol
• 英文别名: (R)-1-phenyl-4,4-dimethylpentan-3-ol；(3R)-4,4-dimethyl-1-phenylpentan-3-ol
• CAS: 821785-10-8
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: VRJGMOZPVOHGFP-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-4,4-dimethyl-1-phenylpentan-3-ol 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (S)-2-((R)-2,2-Dimethyl-1-phenethyl-propoxycarbonylamino)-hexanoic acid
  参考文献：
  名称：

  Design of small molecule ketoamide-based inhibitors of cathepsin K

  摘要：

  A novel series of ketoamide-based inhibitors of cathepsin K has been identified. Modifications to p(2) and p(3) elements were crucial to enhancing inhibitory activity. Although not optimized, a selected inhibitor was effective in attenuating type 1 collagen hydrolysis in a surrogate assay of bone resorption. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.029
• 作为产物：
  描述：

  4,4-二甲基-1-苯基-3-戊酮 在 1-辛硫醇 、 2,4-二硝基苯磺酸二水合物 、 (2S,4S)-(+)-戊二醇 作用下， 以 苯 为溶剂， 反应 3.0h， 以21%的产率得到(R)-4,4-dimethyl-1-phenylpentan-3-ol
  参考文献：
  名称：

  手性抗戊烷-2,4-二醇对布朗斯台德酸催化的酮和酰基硅烷的不对称还原

  摘要：

  通过使用抗-1，3-二醇和催化量（5mol％）的2，4-二硝基苯磺酸在苯中的回流简单方法，将酮和酰基硅烷还原为相应的醇。当使用97％ee的手性戊烷-2,4-二醇时，不对称诱导达到> 99％ee。

  DOI：

  10.1021/ol1006532

文献信息

• Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid
  作者：Jun-ichi Matsuo、Yu Hattori、Mio Hashizume、Hiroyuki Ishibashi

  DOI：10.1016/j.tet.2010.06.012

  日期：2010.8

  Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99%

  通过使用抗-1,3-二醇和催化量的苯中的2,4-二硝基苯磺酸（DNBSA），在回流下将脂肪族酮还原为相应的仲醇。在该介质中加入1-辛硫醇可提高还原效率。通过使用手性抗戊烷-2,4-二醇进行脂族酮的不对称还原，并且在叔烷基酮的还原中观察到高度不对称的诱导作用（最高> 99％ee）。在不存在辛硫醇的情况下，使用手性抗戊烷-2,4-二醇和DNBSA进行的酰基硅烷的不对称还原有效地进行，并以高收率和高ee收率获得了相应的α-甲硅烷基醇。
• Investigation of the Deprotonative Generation and Borylation of Diamine-Ligated α-Lithiated Carbamates and Benzoates by in Situ IR spectroscopy
  作者：Rory C. Mykura、Simon Veth、Ana Varela、Lydia Dewis、Joshua J. Farndon、Eddie L. Myers、Varinder K. Aggarwal

  DOI：10.1021/jacs.8b06871

  日期：2018.11.7

  Diamine-mediated α-deprotonation of O-alkyl carbamates or benzoates with alkyllithium reagents, trapping of the carbanion with organoboron compounds, and 1,2-metalate rearrangement of the resulting boronate complex are the primary steps by which organoboron compounds can be stereoselectively homologated. Although the final step can be easily monitored by 11B NMR spectroscopy, the first two steps, which

  二胺介导的 O-烷基氨基甲酸酯或苯甲酸酯与烷基锂试剂的 α-去质子化、用有机硼化合物捕获碳负离子以及所得硼酸盐络合物的 1,2-金属酸盐重排是有机硼化合物立体选择性同系化的主要步骤。虽然最后一步可以很容易地通过 11B 核磁共振光谱进行监测，但由于需要专门的分析技术，通常在低温下进行的前两个步骤不太为人所知。通过原位红外光谱对这些步骤的研究为优化有机硼化合物的同系化反应提供了宝贵的数据。虽然苯甲酸酯在非配位溶剂中的去质子化比在醚类溶剂中快，氨基甲酸酯的去质子化表现出相反的趋势，这种差异源于氨基甲酸酯与二胺连接的烷基锂试剂形成无活性寄生复合物的倾向。由于在硼-锂交换之前需要将硼上的二醇配体的氧原子与锂离子初始络合，因此在甲苯中大体积二胺配位的锂化物质的硼化反应非常缓慢。然而，醚溶剂或极少量的 THF 通过初始置换与锂离子配位的大体积二胺促进预络合。
• Stereospecific Reaction of α-Carbamoyloxy-2-alkenylboronates and α-Carbamoyloxy-alkylboronates with Grignard Reagents - Synthesis of Highly Enantioenriched Secondary Alcohols
  作者：Dieter Hoppe、Edith Beckmann、Vidya Desai

  DOI：10.1055/s-2004-832835

  日期：——

  Highly enantioenriched secondary alcohols were synthesized by treatment of α-carbamoyloxy-2-alkenylboronates and α-carbamoyloxy-alkylboronates with Grignard reagents. An intermediary boronate complex was transformed stereospecifically to the corresponding secondary 2-alkenyl- and alkylboronates by migration of an introduced residue. Oxidative workup furnished the enantioenriched secondary alcohols.

  高对映体富集的次级醇通过处理α-氨基羧氧基-2-烯烃硼酸酯和α-氨基羧氧基烷基硼酸酯与格林雅试剂合成。中间的硼酸酯络合物通过引入的残基迁移被立体特异性转化为相应的次级2-烯烃和烷基硼酸酯。氧化后处理提供了对映体富集的次级醇。
• Brønsted Acid Catalyzed Asymmetric Reduction of Ketones and Acyl Silanes Using Chiral <i>anti</i>-Pentane-2,4-diol
  作者：Jun-ichi Matsuo、Yu Hattori、Hiroyuki Ishibashi

  DOI：10.1021/ol1006532

  日期：2010.5.21

  Ketones and acyl silanes were reduced to the corresponding alcohols by a simple procedure employing anti-1,3-diol and a catalytic amount (5 mol %) of 2,4-dinitrobenzenesulfonic acid in benzene at reflux. Asymmetric induction reached up to >99% ee when a chiral pentane-2,4-diol of 97% ee was used.

  通过使用抗-1，3-二醇和催化量（5mol％）的2，4-二硝基苯磺酸在苯中的回流简单方法，将酮和酰基硅烷还原为相应的醇。当使用97％ee的手性戊烷-2,4-二醇时，不对称诱导达到> 99％ee。
• Design of small molecule ketoamide-based inhibitors of cathepsin K
  作者：John G. Catalano、David N. Deaton、Stacey T. Long、Robert B. McFadyen、Larry R. Miller、J.Alan Payne、Kevin J. Wells-Knecht、Lois L. Wright

  DOI：10.1016/j.bmcl.2003.11.029

  日期：2004.2

  A novel series of ketoamide-based inhibitors of cathepsin K has been identified. Modifications to p(2) and p(3) elements were crucial to enhancing inhibitory activity. Although not optimized, a selected inhibitor was effective in attenuating type 1 collagen hydrolysis in a surrogate assay of bone resorption. (C) 2003 Elsevier Ltd. All rights reserved.